The Boston Red Sox can get away with not signing Jon Lester to an extension. They'll have options if he walks, something he could very well do after the 2014 season. But since Lester is apparently willing to make like Dustin Pedroia and give the Red Sox a discount on a long-term deal, then, hey, why the heck not? As averse to long-term deals as Ben Cherington's Red Sox seem to be, they should know a good deal when they see one. We'll get to breaking down why soon enough. But first, we need some context. At an awards dinner this week, Lester acknowledged to Peter Abraham of the Boston Globe and others that he's well aware that Clayton Kershaw just got $215 million and Masahiro Tanaka just got $155 million, but he knows signing an extension would mean signing for less than market value. Said the 30-year-old southpaw: I understand to stay here, you’re not going to get a free agent deal. You’re not going to do it. It’s not possible. You’re bidding against one team. I understand you’re going to take a discount to stay. Do I want to do that? Absolutely. But just like [the Red Sox] want it to be fair for them, I want it to be fair for me and my family. If we can get to something in spring training, that would be awesome. Lester added: “I want to win. If that means taking a Pedroia deal [a modest $110 million over eight years] where you stay here for less money to be happy and be competitive and win every year, let’s do it. Let’s get it done.” Now, Cherington must know that he has a wealth of MLB-ready or near-MLB-ready arms waiting in the wings. One of those is Henry Owens, a lefty B/R's Mike Rosenbaum has down as Boston's No. 2 prospect between Jackie Bradley Jr. and Xander Bogaerts. If he's the real deal, he'd be more than a fine replacement for Lester. Another thing Cherington has to know is that next winter's market could be loaded with talented pitchers. Max Scherzer, James Shields, Homer Bailey and Justin Masterson are all slated to be free agents. If the Red Sox don't extend Lester, they could use their riches on somebody else next offseason. However, we can all see how the cost of good pitching is skyrocketing. It's not likely to slow down next winter considering how much talent will be out there. So if the Red Sox sign Lester to a discounted extension now, it's probably going to look like even more of a discount later.